CN109134551B - Water-soluble iron carbonyl compound and preparation method and application thereof - Google Patents
Water-soluble iron carbonyl compound and preparation method and application thereof Download PDFInfo
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- 150000001728 carbonyl compounds Chemical class 0.000 title claims abstract description 23
- 229940087654 iron carbonyl Drugs 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 11
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims description 11
- 229960003151 mercaptamine Drugs 0.000 claims description 11
- 239000002504 physiological saline solution Substances 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 9
- 239000008367 deionised water Substances 0.000 claims description 7
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 238000002329 infrared spectrum Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 239000012153 distilled water Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract description 32
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract description 6
- 231100001231 less toxic Toxicity 0.000 abstract description 2
- JMMPIVZDWBCEFB-UHFFFAOYSA-N cyclopenta-1,3-diene 5-iodocyclopenta-1,3-diene iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.Ic1cc[cH-]c1 JMMPIVZDWBCEFB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004989 dicarbonyl group Chemical group 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- YTGJWQPHMWSCST-UHFFFAOYSA-N Tiopronin Chemical compound CC(S)C(=O)NCC(O)=O YTGJWQPHMWSCST-UHFFFAOYSA-N 0.000 description 4
- 108010058907 Tiopronin Proteins 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- -1 respectively Substances 0.000 description 4
- 229960004402 tiopronin Drugs 0.000 description 4
- 108010054147 Hemoglobins Proteins 0.000 description 3
- 102000001554 Hemoglobins Human genes 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 2
- 238000007405 data analysis Methods 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 108010003320 Carboxyhemoglobin Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/40—Carbon monoxide
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Abstract
本发明公开了一种水溶性铁羰基类化合物，结构式如下所示：
The invention discloses a water-soluble iron carbonyl compound, and the structural formula is as follows:
Description
Technical Field
The invention relates to the field of iron carbonyl compounds. More specifically, the invention relates to a water-soluble iron carbonyl compound, and a preparation method and application thereof.
Background
Carbon monoxide (CO) is a well-known toxic gas, often referred to as a "silent killer. CO can enter the human body by breathing through the lungs, combining with hemoglobin in the blood to form carboxyhemoglobin. The binding force of the compound to hemoglobin is far higher than that of oxygen to hemoglobin (about 230 times, the compound inhibits oxygen from being transported to red blood cells, and oxygen generated by tissues is insufficient, so that the organism can be finally died.
CO is delivered to the relevant body site using CO-containing metal complexes as CO carriers, releasing carbon monoxide molecules in situ, so-called carbon monoxide-releasing agents (CORMs). Most CORMs are transition metal carbonyls. Transition metal carbonyls are a large class of organometallic compounds that under appropriate conditions can lead to the removal of a Carbonyl (CO) group, such as light, substitution reactions, redox induction, and the like. The CO is provided by the CORM through local administration, and does not need to pass through the metabolic process of an organism or a respiratory system; the dosage, the application time and the release speed are easy to control, and the preparation is safer compared with the preparation for directly inhaling CO. However, the water solubility and stability of the CO releasing agent on the market are not good, so that the development of a CO releasing agent with good water solubility and stability is needed.
Disclosure of Invention
The invention provides a water-soluble iron carbonyl compound which can release carbon monoxide. The compound has good water solubility and moderate stability, the metal ions and the organic ligands involved in the reaction also have good biocompatibility, and residues after CO is released are harmless or less toxic to organisms.
In order to achieve the above purpose, the invention provides a water-soluble iron carbonyl compound, the structural formula of which is shown as follows:
the preparation method of the water-soluble iron carbonyl compound comprises the following steps:
with CpFe (CO)2I(Cp＝η5-C5H5) And mercaptoethylamine or tiopronin as raw materials to carry out substitution reaction to obtain a target product.
Preferably, the preparation method of the water-soluble iron carbonyl compound is to prepare CpFe (CO)2I(Cp＝η5-C5H5) And mercaptoethylamine were dissolved in an organic solvent and deionized water, respectively, and an aqueous solution of mercaptoethylamine was added dropwise to the solution containing CpFe (CO)2I(Cp＝η5-C5H5) In organic solution (B), reacting at room temperature, and detecting by infrared spectroscopy to obtain CpFe (CO)2I(Cp＝η5-C5H5) Stopping reaction after disappearance, and separating and purifying to obtain the compound Fe1。
Preferably, the preparation method of the water-soluble iron carbonyl compound is to prepare CpFe (CO)2I(Cp＝η5-C5H5) And tiopronin were dissolved in an organic solvent and deionized water, respectively, and an aqueous solution of tiopronin was added dropwise to CpFe (CO)2I(Cp＝η5-C5H5) And triethylamine (NEt) is added thereto3) Reacting at room temperature, detecting to CpFe (CO) by infrared spectrum2I(Cp＝η5-C5H5) Stopping reaction after disappearance, and separating and purifying to obtain the compound Fe2。
Preferably, the preparation method of the water-soluble iron carbonyl compound, CpFe (CO)2The molar ratio of the I to the mercaptoethylamine is 1: 2-1: 3.
Preferably, the preparation method of the water-soluble iron carbonyl compound, CpFe (CO)2The molar ratio of the I to the mercaptoethylamine to the triethylamine is 1:2: 2-1: 3: 3.
Preferably, the reaction time of the preparation method of the water-soluble iron carbonyl compound is 3-5 hours; the organic solvent is methanol.
Application of the water-soluble iron carbonyl compound in photoinduced CO release.
Preferably, the application of the water-soluble iron carbonyl compound in photoinduced CO release comprises the following specific operation steps:
the compound Fe1Or Fe2Dissolving in 3mL physiological saline, and performing induced release by blue light with wavelength of 470-475 nm.
Preferably, the water-soluble iron carbonyl compound is applied to photoinduced CO release, and deuterium water is used for replacing distilled water for preparation in the preparation process of normal saline; and the compound Fe1Or Fe2The concentration of the compound dissolved in physiological saline is 0.013 mol/L.
The invention at least comprises the following beneficial effects:
(1) the compound has better water solubility and moderate stability;
(2) the metal ions and the organic ligands related to the compound have good biocompatibility;
(3) the compound has easy control of the carbon monoxide releasing time.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention.
Drawings
FIG. 1 shows a compound Fe1A reaction scheme of (1);
FIG. 2 shows a compound Fe2A reaction scheme of (1);
FIG. 3 shows a compound Fe1And Fe2An infrared spectrum of (1);
FIG. 4 shows a compound Fe1The nuclear magnetic resonance hydrogen spectrum of (a);
FIG. 5 shows a compound Fe2The nuclear magnetic resonance hydrogen spectrum of (a);
FIG. 6 Compound Fe1Blue light irradiation degradation map in physiological saline;
FIG. 7 Compound Fe1A relation graph of ln A and time t in the degradation process;
FIG. 8 Compound Fe2Blue light irradiation degradation map in physiological saline;
FIG. 9 Compound Fe2And (3) a relation graph of ln A and time t in the degradation process.
Detailed Description
The present invention is further described in detail below with reference to the attached drawings so that those skilled in the art can implement the invention by referring to the description text.
Preparation of compounds
As shown in FIG. 1, in 30mL of methanol (CH)3OH) to add 303mg of CpFe (CO)2154.30mg of mercaptoethylamine was added to 2mL of deionized water, the aqueous solution was added dropwise to the methanol solution and reacted at room temperature for 5 hours to obtain a red solution, the solvent (methanol and deionized water) was removed by rotary evaporation, and then separation was performed by using a silica gel column, and the eluent was ethyl acetate: methanol 1: 1. Finally, pure red oily substance is prepared, and is temporarily named as compound Fe1
As shown in FIG. 2, in 30mL of methanol (CH)3OH) to add 303mg of CpFe (CO)2I, 326.38mg tiopronin and 250. mu.L triethylamine (NEt) were added to 2mL of deionized water3) The aqueous solution was added dropwise to a methanol solution and reacted at room temperature for 4 hours to give a red solution, the solvent (methanol and deionized water) was removed by rotary evaporation, and then separated on a silica gel column, eluent ethyl acetate: methanol 1: 1. Finally, pure red oily substance is prepared, and is temporarily named as compound Fe2
These two compounds Fe1And Fe2The liquid infrared of (A) is shown in figure 3, wherein the stretching vibration of carbonyl (C ≡ O) is a characteristic absorption peak of the compound, so that the absorption peak is 2033cm-1And 1985cm-1Has a peak of a compound Fe1The stretching vibration peak of the two middle carbonyl groups (C ≡ O) is 2038cm-1And 1991cm-1Has a peak of a compound Fe2The stretching vibration peak of two carbonyl groups (C ≡ O). With electron supply due to the group SRThe difference in the capacity results in the shift of the stretching vibration peak of the carbonyl group (C.ident.O).
Compound Fe1The NMR spectrum of (A) is shown in FIG. 4, and a single peak with a chemical shift of 5.17ppm is assigned to the hydrogen (5H) of the cyclopentadienyl ring (Cp), and a triple peak with a chemical shift of 2.99ppm is assigned to the NCH2Hydrogen of (2.32 ppm), triplet of 2.32ppm ascribed to SCH2Hydrogen (c) in the presence of hydrogen.
Compound Fe2The NMR spectrum of (A) is shown in FIG. 5, wherein a single peak with a chemical shift of 5.16ppm is assigned to the hydrogen (5H) of the cyclopentadienyl ring (Cp), and a single peak with a chemical shift of 3.79ppm is assigned to the NCH2Hydrogen of (3.29-3.30 ppm, multiplet of hydrogen attributed to SCH, two of 2.82-2.84ppm, and two of 1.29-1.41ppm, respectively, to NH3Hydrogen (c) in the presence of hydrogen.
Second, application
Compound Fe1And Fe2Under dark and natural light conditions, the material has good stability, so blue light is selected for carrying out photoinduced CO release on the material.
The prepared compound Fe1(10.1mg,0.04mmol) was added to 3mL of physiological saline, dissolved and added to the reaction tube, and the physiological saline solution was irradiated with blue light at 37 ℃ and measured for infrared (Varian Scimitar 600) at regular intervals.
As shown in FIG. 6, is compound Fe1From the figure, it can be found that the two carbonyl peaks of the compound are 2040cm-1And 1991cm-1As the irradiation time is prolonged, the carbonyl peak is always in the process of decay, and the position of the carbonyl peak is not shifted. The CO release process of the compound is relatively simple, and other iron carbonyl compound intermediates can not appear. The release mechanism is easy to study, thereby guiding the application of the compound in pharmacology.
By 2040cm-1The infrared spectrum data analysis of carbonyl peak shows that the release mechanism of the compound belongs to the first-order kinetic process, and as shown in figure 7, the reaction rate constant and half-life period are respectively 0.0415min-1Half life t1/2＝16.7min。
The prepared compound Fe2(13.5mg,0.04mmol) was added to 3mL of physiological saline and dissolvedAfter the decomposition, the mixture was added to a reaction tube, and the physiological saline solution was irradiated with blue light at 37 ℃ and measured for infrared (Varian Scimitar 600) at regular intervals.
As shown in FIG. 8, is compound Fe2From the figure, it can be found that the two carbonyl peaks of the compound are 2038cm-1And 1990cm-1To form compound Fe1Similarly, the carbonyl peak is constantly in decay with increasing irradiation time and no migration of the position of the carbonyl peak occurs. For 2038cm-1The infrared spectrum data analysis of carbonyl peak shows that the release mechanism of the compound belongs to the first-order kinetic process, as shown in FIG. 9, the reaction rate constant and half-life period are respectively 0.0462min-1Half life t1/2＝15.0min。
For compound Fe1And Fe2The blue light induced release data can be obtained, ln A has a better linear relation with time t, the release of the compounds belongs to first-order reaction kinetics, and the carbonyl release kinetics rates of the two compounds under blue light are nearly the same.
While embodiments of the invention have been described above, it is not limited to the applications set forth in the description and the embodiments, which are fully applicable in various fields of endeavor to which the invention pertains, and further modifications may readily be made by those skilled in the art, it being understood that the invention is not limited to the details shown and described herein without departing from the general concept defined by the appended claims and their equivalents.
Claims (7)
1. The water-soluble iron carbonyl compound is characterized by having a structural formula as follows:
2. a method for preparing a water-soluble iron carbonyl compound according to claim 1, comprising the steps of:
with CpFe (CO)2I. Mercaptoethylamine is used as a raw material to carry out substitution reaction to obtain a target product, which specifically comprises the following steps:
mixing CpFe (CO)2Dissolving mercaptoethylamine and mercaptoethylamine in an organic solvent and deionized water, respectively, and adding the mercaptoethylamine water solution dropwise into the solution containing CpFe (CO)2Reacting in organic solution of I at room temperature, and detecting CpFe (CO) by infrared spectrum2Stopping the reaction after I disappears, and separating and purifying to obtain the compound Fe1，
CpFe (CO)2In I, Cp ═ η5-C5H5。
3. The method of claim 2, wherein CpFe (CO)2The molar ratio of the I to the mercaptoethylamine is 1: 2-1: 3.
4. The method for preparing a water-soluble iron carbonyl compound according to claim 2 or 3, wherein the reaction time is 3 to 5 hours; the organic solvent is methanol.
5. Use of the water-soluble iron carbonyl compound of claim 1 for photoinduced CO release.
6. The application of the water-soluble iron carbonyl compound in the photoinduced CO release as claimed in claim 5, which is characterized by comprising the following specific operation steps:
the compound Fe1Dissolving in physiological saline, and performing induced release with blue light with wavelength of 470-475 nm.
7. The use of the water-soluble iron carbonyl compounds of claim 6 in photoinduced CO release, wherein deuterium water is used to replace distilled water during the preparation of normal saline;
and the compound Fe1The concentration of the compound dissolved in physiological saline is 0.013 mol/L.
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| CN115010939B (en) * | 2022-04-22 | 2023-04-28 | 深圳先进技术研究院 | Carbonyl siderophore capable of responding to release of carbon monoxide and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102850403A (en) * | 2012-05-29 | 2013-01-02 | 嘉兴学院 | Water-soluble iron carbonyl compound, and preparation method and application thereof |
| CN104814952A (en) * | 2015-04-16 | 2015-08-05 | 嘉兴学院 | Method for promoting carbon monoxide release of carbon monoxide-releasing molecules and preventing sedimentation |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102850403A (en) * | 2012-05-29 | 2013-01-02 | 嘉兴学院 | Water-soluble iron carbonyl compound, and preparation method and application thereof |
| CN104814952A (en) * | 2015-04-16 | 2015-08-05 | 嘉兴学院 | Method for promoting carbon monoxide release of carbon monoxide-releasing molecules and preventing sedimentation |
Non-Patent Citations (4)
| Title |
|---|
| Dicarbonyl-bis(cysteamine)iron(II): A light induced carbon monoxide releasing molecule based on iron(CORM-S1);Robert Kretschmer et al.;《Journal of Inorganic Biochemistry》;20101015;第105卷;第7页左栏第2段，Scheme 2 * |
| 姜秀娟等.铁羰基化合物一氧化碳释放剂及其释放研究.《"一带一路，引领西部发展"-2017年中西部地区无机化学化工学术研讨会论文摘要》.2017, * |
| 水溶性铁羰基化合物的合成及羰基释放动力学研究;李小菲等;《上海化工》;20161215;第41卷(第12期);图1，摘要，第15页左栏第3-4段 * |
| 铁羰基化合物一氧化碳释放剂及其释放研究;姜秀娟等;《"一带一路，引领西部发展"-2017年中西部地区无机化学化工学术研讨会论文摘要》;20170430;图1、57页第2段 * |
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